Life Lessons From “Four Billionaires and a Parking Attendant”: A Q&A with Chris Ullman

Philanthropy Roundtable recently interviewed Chris Ullman, former communications director at global investment firm The Carlyle Group, about his new book, “Four Billionaires and a Parking Attendant: Success Strategies of the Wealthy, Powerful, and Just Plain Wise.”  

In this book, Ullman shares lessons he learned while working alongside four billionaires and more than a dozen of the most successful people in the world, including his former boss, David Rubenstein. Through his observations of these powerful people and their philanthropy, as well as a parking attendant who taught him about happiness, Ullman creates a blueprint for living your best possible life filled with purpose and humility.  

The interview below has been edited for length and clarity.  

Q: Can you share a bit about your background and what inspired you to write this book? What are you hoping readers learn from it?  

Ullman: For 37 years I’ve done political and corporate communications in Washington, D.C. For 25 of those years, I’ve mentored college students through an intern program managed by The Fund for American Studies. I help the students position themselves for success in the workplace using proven communications and marketing skills and practices. In this book, I share anecdotes for how to think and behave to be one’s best, gathered from the wealthy and powerful bosses I’ve had in my career. There are 50 lessons from 15 people, including four billionaires, top government officials and corporate executives. I also include a parking attendant who taught me about happiness. 

Q: You said you have had the pleasure of working with several billionaires and titans of achievement in your lifetime. In your opinion, what kinds of success strategies do the people profiled in your book have in common?  

Ullman: Every uber-successful person featured shares a common trait: they are purposeful. As a result, they have a plan, vision or dream they are driving toward. If they were sailboats, their sails would be taut, not limp. Other traits they share include: they go over, around or through obstacles; they pivot quickly to solution mode with no unnecessary hand-wringing about life being unfair; they work long hours; they are also hopeful and a little crazy. 

Q: Your book also includes eight strategies for success that comprise lessons and ideas you’ve learned from people you’ve met. Can you summarize a few of your strategies?  

Ullman: This book is about being your best, not being the best. We all have God-given gifts, and the key is to develop and harness them to find personal fulfillment and to help other people on their journeys. Readers will learn about finding purpose, being grateful, thinking strategically, being humble, building bridges and getting around obstacles. 

One of my favorite lessons is called Confident Joy. I learned it from Adena Friedman, who was The Carlyle Group’s chief financial officer, and is now the CEO and chair of the board of directors at Nasdaq. One quarter, not long after Carlyle became a public company, the firm’s earnings were lackluster. To get senior executives to be a bit happier when talking to Wall Street analysts on the earnings call, Adena tried to get them to wear T-shirts with big happy faces on them. That’s the joy part.  

When all the executives rejected the shirts, she didn’t shrink or crumble in the face of corporate peer pressure. This is the confidence part. She kept her T-shirt on and did the earnings call and never mentioned it again. That greatly inspired me because peer pressure can be a very stifling thing. 

Q: You’ve worked directly for billionaire David Rubenstein at The Carlyle Group, and you talk a lot about his philanthropy, particularly his “patriotic philanthropy.”  What is his approach to charitable giving, and why does it stand out to you? 

Ullman: David is a strategic philanthropist. By targeting his giving and having specific criteria, he is more efficient and focused in his philanthropy. His giving criteria include gifts that will kick-start a project or bring it to fruition, and organizations and projects that excite him intellectually to which he will dedicate money and time. 

He also has a thoughtful framework that helps him sort through countless giving opportunities: 

  1. Be narrow: Give larger amounts to fewer organizations. 
  2. Go small: Be the big fish in the small pond. 
  3. Have impact: Leverage gifts by getting other people to give. 
  4. Make human connections: Deploy the money as close to the final recipients as possible. 

Here are his three reasons for giving away money: 

  1. You might actually do some good. 
  2. It hurts as you write the check, but always feels good afterward. 
  3. Though you can’t buy your way into heaven, why take a chance. 

David coined the phrase “patriotic philanthropy,” which means giving to organizations that preserve the history and heritage of America. As he says, this category actually receives fewer dollars than his other giving categories but generates more attention. How could it not, when you’re paying for pandas at the National Zoo or repairing the Washington Monument after an earthquake? 

Q: Philanthropic giving is a priority for some of the other people profiled in the book as well. What takeaways can you offer the Roundtable donor community about how these people do philanthropy well? 

Ullman: I’ve been very impressed with how Bill Conway, the billionaire co-founder and co-chairman of Carlyle, approaches his philanthropy. His Catholic faith has had a huge impact on his giving priorities, which center on human needs. 

For many years, Bill went to daily Mass at the church near Carlyle’s offices. Along the way homeless people would ask him for money. Bill ignored them for a long time but eventually talked to them. Once Bill found out their names, he could no longer ignore them. This led, at first, to small gifts to So Others Might Eat (SOME), the nonprofit that helps people in need in Washington, D.C. Then came the gifts with six zeros on them. 

As one of the best investors in the world, Bill approached helping people in need the same way he’d create value in a Carlyle portfolio company: start with the basics and move to the complex. For a human, that means food, clothing, shelter and medical care. Then education, job training and job placement.  

As he continued to help SOME, he embarked on a new front focused on getting people jobs in nursing. Bill’s wife was a nurse earlier in her career, so they knew the profession well and its many benefits—solid pay, flexible hours, job portability. 

Bill researched a number of nursing schools, picked several, and made multimillion-dollar gifts targeted at scholarships for lower income students. His goal was to help them get a degree, get a job and have a better shot at a fulfilling career and a more secure life. He’s given hundreds of millions of dollars at this point with more in the pipeline. 

Q: What do you think stands in the way of people being their best? 

Ullman: Two things: ego and lack of purpose. The problem with ego is that it fosters tunnel vision: my way is the best way, if not the only way. Big egos are averse to others’ ideas. I’ve seen this in action throughout my career. It’s sad, and wholly unnecessary. 

Meanwhile, the premise of this book is that there is wisdom all around us. The key is to be observant and open to new ways of thinking. The lesson “Think Like Your Successor Every Day” sums this up well. Arthur Levitt, the former chairman of the Securities and Exchange Commission, came to work every day with new ideas. He wanted to embrace change and be in constant forward motion. Why wait, he told me, for your successor to get rid of tired ways of doing things. Every day we should take a fresh look at our practices and habits. Keep the good ones and discard the ineffective ones, Arthur believed and practiced. 

Lack of purpose is a particularly unfortunate state of being. I’ve met many young people in their early 20s who have no idea what they want to do with their lives. I remind them that one-quarter of their lives is over, and they better get going. 

People with purpose are focused, act with intent and get stuff done. They have a good sense of where they are going and how to get there. As my late father told me many times growing up, “This is not a dress rehearsal. Get on with your life.” The first “strategy” in the book is about being purposeful. There’s a lesson learned from John Kasich, former House Budget Committee Chairman, called “Act Like You’re Relevant, Even When You’re Not.” It’s about playing the game, not sitting on the sidelines. Life is difficult. Life is beautiful. Life is short. Stop complaining, come up with a plan, and make your little part of the world a better place. 

Q: Can you tell us how you met the parking attendant, Selah, and how he contributed to your book? 

Ullman: One of the most important lessons in the book – about choosing to be happy – is from a parking attendant, not a billionaire. David Rubenstein says he doesn’t know many happy rich people, and many are tortured souls, he says. Saleh Awolreshid is an Ethiopian immigrant. Every day for four years he parked my car. Despite heat in the summer and cold in the winter, he was happy. That so impressed me. And it was a fascinating contrast with the billionaires and other wealthy people 40 feet above in Carlyle’s beautiful offices. Saleh chose to be happy. He was grateful for what he had: family, a job, being in America. Wow! 

Q: There are so many books on the market with financial advice. What sets your book apart? 

Ullman: Most books about how to be successful are by billionaires who tell you how they did it or academics who interviewed billionaires and tell you how they did it. My book is unique in that I worked hand-in-glove with these people, observed them in action, absorbed their secrets, and am now sharing those ways of thinking and behaving that foster success. Importantly, none of this is rocket science. The key is being humble and having a desire to be your best. 

Q: At the end of the book, you have a list of ten things not to do. What are a few “don’ts” that resonate with you? 

Ullman: Wealthy and powerful people may have lots of wealth and power, but they are people in the end, filled with faults and imperfections, just like the rest of us mere mortals. So, while I learned an immense amount of good things, I also learned a bunch of things not to do. Some of the best ones: Don’t be arbitrary – facts and logic matter. Don’t bow down to the committee – groupthink is real, powerful, comforting and rarely bold or courageous. Don’t confuse movement with progress – walking in a circle may burn calories but it doesn’t get you closer to your destination. 

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